Process of treating polyester fibers with resins

ABSTRACT

A process for the resin treatment of polyester fibers comprising treating the fibers with a compound having the structural formula selected from the group consisting of   AND SUBSEQUENTLY TREATING THE RESULTING FIBERS WITH A RESIN CONTAINING -COOCH CH2 radical, said resin having water-and-oilrepellences and antistatic property, in the presence of reaction initiators. This process is capable of applying resins excellent in friction resistance and washing resistance to polyester fibers.

United States Patent 91 Esaki et al.

[451 Sept. 2, 1975 1 PROCESS OF TREATING POLYESTER FIBERS WITH RESINS [75] Inventors: Ikuji Esaki; Yoshihiro Chikamatsu,

both of Gifu, Japan [52] US. Cl. 427/202; 427/407; 427/412; 428/270; 428/272; 428/274 [51] Int. Cl. D06C 29/00 [58] Field of Search 117/76 T, 76 R, 138.8 F, 117/1355, 62.1, 62.2; 108/115.6; 252/86; 8/D1G. 18

[56] References Cited UNITED STATES PATENTS 3,061,473 lO/l962 Tesoro 117/1355 3,236,685 2/1966 Caldwell et al. 1. 117/1388 3,521,993 7/1970 Swidler et al 8/1156 3,574,620 4/1971 Tesoro l17/62.l

Primary Examiner-Cameron K. Weiffenbach Assistant Examiner-Ralph E. Varndell Attorney, Agent, or F irml-laseltine, Lake & Waters [5 7] ABSTRACT A process for the resin treatment of polyester fibers comprising treating the fibers with a compound having the structural formula selected from the group consisting of and subsequently treating the resulting fibers with a resin containing COOCH Cl-l radical, said resin having water-and-oil-repellences and antistatic propcity, in the presence of reaction initiators. This process is capable of applying resins excellent in friction resistance and washing resistance to polyester fibers.

4 Claims, No Drawings PROCESS OF TREATING POLYESTER FIBERS WITH RESINS BACKGROUND OF THE INVENTION The present invention relates to a process of applying resins having excellent friction resistance and washing resistance to polyester fibers.

The polyester fibers are usually subjected to resin treatment in order to impart thereto a water repellenee, an oil repellence and an antistatic property. Moreover, to ensure that the treated fibers have good water and oil repellences and antistatic property, the resin to be applied is required to have excellent friction resistance and washing resistance.

In order to impart to the polyester fibers water and oil repellences and antistatic property, there has been heretofore practiced a process which comprises treating directly the fibers with resins having water and oil repellences and antistatic property.

However, the resins which have been applied to the polyester fibers using such a known treating process are poor in friction resistance and washing resistance, whereby the treated fibers are incapable of maintaining good water and oil repellences and antistatic property to a sufficient degree.

SUMMARY OF THE INVENTION It is an object of the present invention to remove the aforementioned disadvantages and to provide an improved process of resin treatment.

lt is another object of the present invention to provide a process for the resin treatment of polyester fibers which comprises applying resins excellent in friction resistance and washing resistance to the fibers, thereby imparting good water and oil repellences and antistatic property thereto.

In accordance with the present invention, the above objects can be accomplished by providing a process for the resin treatment of polyester fibers which comprises treating the fibers with a compound having the structural formula selected from the group consisting of (benzoyl acrylic acid) I? c on Cl? coon and -CH (3H coon,

(# -anthra ui none acrylic acid) and subsequently treating the resulting fibers with a resin containing COOCH CH: radical in the presence of reaction initiators.

DETAILED DESCRIPTION OF THE INVENTION The present invention includes firstly treating the polyester with a compound having the structural formula selected from the group consisting of -C-CH= The polyester fibers so treated fixedly adhere to the moiety of due to their affinity, whereby the polyester fibers and the compounds are firmly bonded.

Such a treatment may be conducted by contacting the polyester fibers with the above-mentioned compounds using a variety of means. For example, when the polyester fibers are dyed, the fibers are contacted with the compounds in a dyeing bath containing the compound added thereto under high temperature and pressure dyeing conditions or normal temperature carrier dyeing conditions, or the compound is sublimed to be brought into contact with the fibers.

The polyester fibers used in the present invention include the cloth or yarn of polyester fibers, or the mixed spun or woven cloth or mixed yarn of polyester fibers and other fibers.

The above-mentioned compounds used in the present invention may be one or two members selected from the above-mentioned group. Although the amount of these compounds used may be optionally determined, it is preferably in the range of from 0.1% to 1.0% by weight with respect to the amount of the polyester fiber to be treated.

According to the present invention, the fibers result ing from the first treating process are subsequently treated with a resin having COOCH=CH radical, said resin having water and oil repellences and antistatic property, in the presence of reaction initiators.

In so treating, the moiety of CH=CH.COOH which was bonded to the polyester fibers and the COOCH=CH radical in the above resin are bonded together in the presence of reaction initiators, whereby the polyester fibers are firmly bonded with the resin containing the COOCH=CH radical through the compounds.

This treatment is also conducted by means of the conventional known resin treatment method.

In this manner, it is possible to apply a resin having excellent friction resistance and washing resistance to the polyestor fibers according to the present invention, thereby permitting the impartment of satisfactory water and oil repellences and antistatic property to the cocll=cll. for example, those available under the commercial names Zoron FR (obtained from E. I. du Pont de Nemours & Co. USA) and Scotchguard PC 208" (Sumitomo Three M Co. Ltd., Japan).

In addition, a hand controlling agent, softener, antistatic aiding agent, catalyst and the like may also be used. For example, those available under the commercial names; Sumitex resin 8008 and Sumitex resin M-3 (Sumitomo Chemical Co., Japan), Permax (Yoshimura Petrochemical, Co., Japan), TH 44 (Nikka Chemical Co., Japan), softex K206 (Kao- Atlas Co., Japan), Catalyst 0 (Japan-Reichhold Co., Japan) may be used.

The present invention will fully described by the following examples.

EXAMPLE 1 As a polyester fiber, a plain fabric of 100% processed yarn which has been subjected to refining and heat set is used.

Table 1 Continued CH CH l 0.2% coon The percentage is weight percent on the basis of the weight of the fabric.

After immersing, the fabric is washed with water and dried. The so-treated fabric is called a sample NO. A.

Also, the same procedures as indicated above are carried using a dyeing solution consisting of the above composition containing no compound CH (fl-I COOH ll The resulting fabric is called a sample NO. B.

Then, the sample NO.A and NOB fabrics each are treated with the respective resin solutions containing the following compositions indicated in Table II.

Each of the fabrics NO.A (A-I, A-Il) and NOB (8-1, 8-") so treated is wrung to a 0.70% degree, dried with a hot air at a temperature of 100C for 3 minutes and further heat treated at 150C for 3 minutes and then washed with a hot water and finally dried.

The resin treated fabrics are subjected to laundry treatment, dry cleaning treatment and friction treatment, after which they are tested for water repellence, oil repellenee and electrification. The results are shown in Table III.

Table III Water Repellence Dry cleaning 2 3 4 Friction contacting the fabric with the compound CH (fl-I COOH Table l Color index Disper Blue 71 0.2% Color index Disper Red 54 0.3% Color index Disper Yellow 13 1.271 Dispersing agent 0.5g/l pH controlling agent 0.1cc/l (acetic acid) Test item Test method Test number Sample NO.A A 1 A ll Sample NO.B B I Table Ill-Continued Test item Oil Repellence Test method Laundry Dry cleaning Friction Test number I 2 3 4 l 2 3 4 5 50 100 200 Sample NO.A

A l 4 4 4 4 4 4 4 4 4 4 4 4 4 A ll 4 4 4 4 4 4 4 4 4 4 4 4 4 Sample NOB B I 3 3 2 2 2 3 2 2 2 2 2 2 2 B ll 3 3 2 2 2 3 2 2 2 2 2 2 2 Test item Electrification (V) Test method Laundry Dry cleaning Test number I 2 3 4 5 l 2 3 4 5 Sample NO.A

A l 80 l I I30 190 200 30 90 140 100 180 A 3 ll 70 I50 200 230 200 40 70 50 I20 230 Sample NOB B l 300 510 720 1 I00 2000 170 430 700 800 1260 B II 420 690 I210 l580 I690 280 530 i410 2300 1900 These tests were carried out according to the following procedures. Water repellence test procedure The water repellence is determined according to .118 LlO79 chemical fiber fabric test method 5, 24, 2 water repellence A procedure (a spray method). With regard to evaluation, the maximum is 100 and the minimum is 0 and the values not less than 70 to 80 are good. Oil repellence test procedure Machine oil method: one drop (about ().05g) of machine oil (JIS K22l4l) is fallen on the sample with a micro spertel, and repellence is determined by the following evaluations. The evaluations of no less than 4 represent a good repellence. Grade Condition of machine oil adherence 1 Machine oil is sucked into the sample within a few seconds when dropped thereon. 2 The drop configuration is crushed, but a portion thereof is remained liquid on the surface of the sample. 3 The contact angle between machine oil and the sample is below 90. 4 The contact angle between machine oil and the sample is above 90 and when the machine oil is sucked up after leaving for 15 minutes a slight adherence is observed. 5 The contact angle between machine oil and the sample is above 90 and when the machine oil is sucked up after leaving for IS minutes no adherence is observed. Method of determining electric charge voltage Four sheets of the sample (3cm X about 30cm) are attached separately from each other to the stationary part of a rotary staticktester, while a sheet of nylong plain fabric (2.5cm X about cm) is fixed under said staticktester in the transverse direction with respect to the direction of rotation to contact with said four sheets upon rotation for a friction reference. The rotor is rotated at 800 rpm under load of 500g for 60 records. Then, each of the samples tested is determined for friction electrification voltage (V), and the voltage V is divided by 8 to give an electrification voltage per a sheet of the sample. Friction method Gakushin type of fastness to friction tester is used, and the surface of the sample is rubbed forward and backward with cotton cloth (3 cm X 12cm) for 50, 100, 150, 200 times. Laundry method The sample is placed in an automatic reverse type of an electric washing machine containing 0.5% detergent at a temperature of 40C and stirred and washed for 30 minutes. After washing, the sample was centrifugally dehydrated and dried. This is one cycle.

Dry cleaning method About six sheets of the sample (20 cm X 10 cm) are placed in a cylindrical pot having a diameter of 10 cm and a height of 15 cm and containing ll of perchloroethylene. Four of the pots are attached to the same rotating axis and the rotating axis is rotated at ambient temperatures and at 42 i 2 rpm for 30 minutes. At the end of the period, the samples are removed from the pots and naturally dried. This is one cycle.

As is apparent from Table III, the samples (A l, A II) resintreated according to the process of the present invention are more excellent in water repellence, oil repellence, antistatic property than the samples (B I, B ll) treated according to the conventional method.

EXAMPLE 2 As a polyester fiber, a mixed woven plain fabric of polyester filament and 20% rayon is used.

The fabric is dyed by immersing it in a dyeing solution consisting of the composition indicated in Table IV below and having a pH value of 5 to 6 at a temperature of C for about 60 minutes while simultaneously Table V NO. C NO. D

().l 2.5 LO [.0

Sumitex resin M-3 Catalyst 0 Zoron FR Permax 25 Softex K206 Ammonium persulfate The fabrics thus resin-treated are respectively subjectcd to laundry treatment, dry cleaning treatment and friction treatment, after which they are tested for water repellence, oil repellence and electrification. The results are shown in Table VI.

Table VI Table VII 0 ll -C-CH=CH OOH l (weight percent on the basis of the weight of the fabric) appropriate amount I00 cc Emulsifying agent Water After immersing, the fabric is dried at 100C, and further dried at 180C for 2 minutes. The resulting fabric is called a sample NO. E.

Then. the sample NO. E fabric is treated with the resin solution consisting of the composition indicated in Table VIII.

Test item Test method Test number Water repellence Dry cleaning 3 Laundry 2 3 4 2 4 Friction l 00 Oil repellence Dry cleaning 2 4 Sample NO. C Sample NO. D

Test item Test method Test number Sample NO. C Sample NO. D

Laundry l NALII bil 'w-l b NAJI Test item Electrification V) Test method Test number Sample NO. C Sample NO. D

dry

Laun 2 l Friction l 00 Dry cleaning The tests are carried out according to the same procedures as those described in Example 1.

As is apparent from Table VI, the sample (NO. C) resin-treated according to the process of the present invention is more excellent in water repellence, oil repellence and antistatic property than the sample (NO.

D) treated according to the conventional process. Ex-

ample 3 A plain fabric composed of 100% polyester is im mersed in a treating solution consisting of the composition indicated in Table VII below while simultaneously Table VIII Sumitex resin 800$ L09? Catalyst 0 0. I71 Zoron FR 2.8% Permax 25 1.0% TH 44 1.0% Ammonium persulfate 0.03%

The fabric thus resin-treated is subjected to laundry treatment, dry cleaning treatment and friction treatment, after which it is tested for water repellence, oil repellence and electrification. The results are shown in contacting the fabric with the compound Table IX.

Table IX Test item Water repellence Test method Laundry Dry cleaning Friction Test number I 2 3 4 5 l 2 3 4 5 50 I00 200 Sample NO. E 90 9O 9O 8O 9O 9O 8O 8O 80 9O 9O 80 Test item Oil repellence Test method Laundry Dry cleaning Friction Test number I 2 3 4 l 2 3 4 5 50 I00 200 Sample NO. E 4 4 4 4 4 4 4 4 4 4 4 4 4 The tests are carried out according to the same pro- 2. The process according to claim 1 wherein the cedures as those described in Example 1. amount of the compound used is in the range of 0.1%

As is apparent from Table lX, the sample NO. E reto 1.0% by weight of the polyester fiber to be treated. sin-treated according to the process of the present in- 3. The process according to claim lwherein the reacvention is excellent in both water repellence and oil retion initiator is benzoyl peroxide or ammonium persulpellence. fate.

The fabrics of Example I, 2 and 3 which are treated 4, A i l f manufacture i i according to the present invention possess satisfactory a polyester fabri substrate, d Water-and oil'repellences and antistatic p yb. a coating thereon, said coating comprising a comln view of the foregoing, it is concluded that the propound i h a CH CH COOH moiety having cess of the Plelsent inVentiQn is capable of pp y the structural formula selected from the group conins excellent in friction resistance and washing resis- Sisting f tance to polyester fibers.

What is claimed is: t 1. A process for improving the water and oil repel- 5 lences and antistatic properties of polyester fibers which comprises coating said fibers with a compound having a CH CH COOH radical selected from COOH the group consisting of CH= H and - C CH ('11-! COOH and

' CH CH I o o coon IA and reacting the thus-coated fiber with a fluorine resin l containing a COOCH CH radical having waterand oil repellences and antistatic properties in the presgroups of said compound, and a fluorine-containing ence of a reaction iniator thereby to bond said resin to resin having a COOCH CH radical attached to said thustreated fiber by reaction between said radisaid compound through said moiety.

cals of said compound and said resin. 

1. A PROCESS FOR IMPROVING THE WATER AND OIL REPELLENCES AND ANTISTATIC PROPERTIES OF POLYESTER FIBERS WHICH COMPRISES COATING SAID FIBERS WITH A COMPOUND HAVING A - CH = CH COOH RADICAL SELECTED FROM THE GROUP CONSISTING OF
 2. The process according to claim 1 wherein the amount of the compound used is in the range of 0.1% to 1.0% by weight of the polyester fiber to be treated.
 3. The process according to claim 1 wherein the reaction initiator is benzoyl peroxide or ammonium persulfate.
 4. An article of manufacture comprising: a. a polyester fabric substrate, and b. a coating thereon, said coating comprising a compound with a - CH CH - COOH moiety having the structural formula selected from the group consisting of 